Organozinc synthesis

An organozinc compound that occupies a special niche in organic synthesis is iodo-methylzinc iodide (ICH2ZnI). It is prepared by the reaction of zinc-copper couple [Zn(Cu), zinc that has had its surface activated with a little copper] with diiodomethane in diethyl ether. 

Synthesis of heterocycles with participation of organozinc compounds 98T8275. 

The procedure in Section C is representative of the synthesis of non-natural a-amino acids featuring the palladium cross coupling reaction of a (1-alaninc organozinc derivative with aromatic electrophiles. This methodology has been successfully extended with modifications to both the electrophile and the catalyst as shown in the Table. 

E. Erdik, in Organozinc Reagents in Organic Synthesis, CRC Press, Boca Raton, 1996. 

Luche and coworkers extended their studies on the applications of ultrasound to synthesis to include a variety of systems. Among these applications are the syntheses of lithioorganocuprates(ll), of aldehydes from formamides(12), of organozinc intermediates(13),... 

Because of the separation of this chapter into fundamental synthetic and structural aspects of organozinc compounds and the applications of these compounds in organic synthesis, many topics are treated twice, but with decidedly different emphases. By way of example, the important organozinc alkoxides are covered first in the inorganometallic section, where the emphasis is on their syntheses, structures, and applications other than in organic synthesis. Later, in Section 2.06.16.2, the uses of such compounds as chiral catalysts in asymmetric addition reactions are discussed. 

The introduction of cyano groups in the 3-position of diketimiminate ligands greatly increased the crystallinity of their complexes (Figure 49, 95), due to the formation of one-dimensional coordination polymers. A new f3-oxo-<5-diimine ligand, in turn, allowed the synthesis of a bimetallic organozinc complex 96, by the same methods that had been used for the syntheses of the mononuclear species 92-94.154... 

Downs et al. reported the synthesis of methylzinc tetrahydridoborate 164 by the two routes shown in Scheme 99.230 The compound is an extremely moisture and oxygen sensitive, colorless, polycrystalline solid, whose solid-state structure was determined by X-ray analysis. Figure 76 shows that 164 consists of helical polymers of alternating methylzinc and tetrahydridoborate ions. The zinc atom is formally pentacoordinate, making this one of the few organozinc compounds with five-coordinate zinc atom. 

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